DE302737C - - Google Patents
Info
- Publication number
- DE302737C DE302737C DENDAT302737D DE302737DA DE302737C DE 302737 C DE302737 C DE 302737C DE NDAT302737 D DENDAT302737 D DE NDAT302737D DE 302737D A DE302737D A DE 302737DA DE 302737 C DE302737 C DE 302737C
- Authority
- DE
- Germany
- Prior art keywords
- oxymethylene
- tropic acid
- ether
- ester
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- -1 Oxymethylene phenyl acetic ester Chemical compound 0.000 claims description 12
- JACRWUWPXAESPB-QMMMGPOBSA-N Tropic acid Natural products OC[C@H](C(O)=O)C1=CC=CC=C1 JACRWUWPXAESPB-QMMMGPOBSA-N 0.000 claims description 12
- VBSTXRUAXCTZBQ-UHFFFAOYSA-N 1-hexyl-4-phenylpiperazine Chemical compound C1CN(CCCCCC)CCN1C1=CC=CC=C1 VBSTXRUAXCTZBQ-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 8
- 235000019439 ethyl acetate Nutrition 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 229940049953 phenylacetate Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229930003347 Atropine Natural products 0.000 description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
- 229960000396 atropine Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- QFKJCKFAYFUXRQ-UHFFFAOYSA-N barium;hydrate Chemical compound O.[Ba] QFKJCKFAYFUXRQ-UHFFFAOYSA-N 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE302737C true DE302737C (enrdf_load_stackoverflow) |
Family
ID=556514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT302737D Active DE302737C (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE302737C (enrdf_load_stackoverflow) |
-
0
- DE DENDAT302737D patent/DE302737C/de active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE302737C (enrdf_load_stackoverflow) | ||
| DE668489C (de) | Verfahren zur Darstellung von 2, 4-Dioxo-3, 3-dialkyltetrahydropyridin-6-carbonsaeureestern bzw. der entsprechenden freien Saeuren | |
| DE946804C (de) | Verfahren zur Herstellung von schwefelhaltigen Abkoemmlingen der Barbitursaeure | |
| DE213155C (enrdf_load_stackoverflow) | ||
| DE613403C (de) | Verfahren zur Darstellung am Kohlenstoff und am Stickstoff substituierter Barbitursaeuren | |
| DE2314676C3 (de) | Verfahren zur Herstellung von 2-Phenyl-5-benzothiazolylessigsäure und deren Salzen | |
| DE1445426C (de) | Verfahren zur Herstellnng von Den vaten der 2 Thiobarbitursaure | |
| AT228407B (de) | Verfahren zur Herstellung neuer Ester von N-(Hydroxyalkyl)-nortropanen bzw. -norgranatanen, deren Salzen und quartären Ammoniumverbindungen | |
| DE575470C (de) | Verfahren zur Darstellung von C, C-disubstituierten Derivaten der Barbitursaeure | |
| AT218519B (de) | Verfahren zur Herstellung von neuen Pyrazol-Derivaten | |
| AT142914B (de) | Verfahren zur Darstellung von ß-Jodnaphtholdisulfonsäuren. | |
| CH360999A (de) | Verfahren zur Herstellung von heterocyclischen Carbonsäuren der Pyrazolreihe sowie ihren Estern | |
| DE951364C (de) | Verfahren zur Herstellung von schwefelhaltigen Abkoemmlingen der Barbitursaeure | |
| AT213896B (de) | Verfahren zur Herstellung von neuen, basisch substituierten Thioäthern von Pyrimidinen | |
| DE1620529B1 (de) | Verfahren zur Herstellung von 2-(3-Hydroxy-5-hydroxymethyl-2-methyl-4-pyridyl)-tetrahydro-1,3-thiazin-4-carbonsäure | |
| CH356440A (de) | Palladiumschwamm-Katalysator | |
| CH174913A (de) | Verfahren zur Darstellung von Acetyltropasäure-2,2-dimethyl-3-diäthylaminopropanolester. | |
| DE1793261A1 (de) | ss-Phenyl-acrylsaeurenitrile | |
| DE1135918B (de) | Verfahren zur Herstellung von 6-Chlor-7-sulfamyl-1, 2, 4-benzothiadiazin-1, 1-dioxyden | |
| CH382183A (de) | Verfahren zur Herstellung von a-Amino-B-hydroxycarbonsäuren | |
| DE1076116B (de) | Verfahren zur Herstellung von therapeutisch wirksamen ª‰-Oxy-carbonsaeureamiden | |
| DE1026320B (de) | Verfahren zur Herstellung von 5, 5-disubstituierten 3-Amino-hydantoinen | |
| DE3018963A1 (de) | Verfahren zur herstellung von v-triazolyl-(2)-phenolen | |
| DE1067826B (de) | Verfahren zur Herstellung von Jodthyroninderivaten | |
| DE1545833A1 (de) | Verfahren zur Herstellung von Pyridobenzimidazolcarbonsaeuren |